Menthol compound.



' doctor of hilosophy, chemist, a citizen of the or ELBERFELD, GERMANY,ASSIGNOR To FARBEN- RUDOLPH BERENDES,

FABRIKEN VORM. FRIEDR. BAYER & (30., OF. ELBERFELD, GERMANY,

A CORPORATION OF GERMANY.-

,IVIENTHOL COMPOUND.

Specification of Letters Patent.

rammed Nov. 27, 1906.

' Application filed June as, 1906'. Serial m.-s2s.1s4..

To all whom it may concern.-

Be it known that I, Rrmoprn BERENDEs,

German mpire, residing at Elberfeld, Kingdom of Prussia, Germany, haveinvented new and useful Improvements in New Menthol Compounds, of whichthe following is a specificatlon.

My invention relates to the production of" new pharmaceutical productswhich are chemically alkylox lacetyl compounds of menthol, andwhiclilaccording to my researches possess valuable therapeuticproperties, being valuable substitutes for menthol without the intenseodor and the'oad secondary efiects of this compound. They are.especially qualified for the treatment of migrain, nervous headache,catarrhal affections, &c., and the absence of any odor andtaste andtheir ability of being easil split up into menthol render their outwardand internal application highly satisfactory, an average dose being from0.1 to 1.0 grams.

The process for producing the new comoundsconsists in treating mentholwith alyloxy acetic acids or derivatives thereofsuch as ethoxy or methoxacetic acid, ethoxy acetyl chlorid, or the l1ke-in such manner as toroduce esterification. The new products t us produced are colorlessliquids soluble in alcohol and ether. When reacted upon by dilutecaustic alkalies, they are split up into alkyloxy acetic acid andmenthol.

In carrying out my process practically I can roceed as follows, the artsbeing by Weig t: One hundred and ty-six parts of menthol andseventy-nine parts of p r1d1n are dissolved in five hundred parts 0benzene, and to the resulting solution one hundred and, twent -two andone-half parts of ethoxy acetyl c lorid are added. After the chlorid hasentered into reaction the mixture is shaken with dilute h drochloricacid,which will extract the pyridm, and afterward with water. Thebenzenesolution is then separated from the water and dried. The benzene isdriven oif and the residue is distilled in 'vacuo.

The new com ound thus obtained having the formula'C ,,OCOCH O0 H is alimpid oil which boils at 153 centigrade under a pressure of abouttwenty millimeters.

when-reacted upon by dilute caustic alkalies. The process is carried outin an analogous manner on using other alkyloxy acetic acids orderivativesthereof, such as methox acetic acid, methoxy acetyl chlorid,or the li e.

Having now described my invention and in what manner the sameis to beperformed, what I claim as new, and desire to secure by Letters Patent,is-

1. The herein-described new alkyloxy acetyl compounds of menthol,obtainable by the action of alkyloxy acet l chlorid on menthol, beingcolorless liquid s soluble in ether and alcohol; liberating the mentholwhen reacted upon by dilute caustic alkali-es and exhibiting valuabletherapeutic properties, substantially as hereinbefore described;

my hand in the presence of two subscribing witnesses.

' RUDOLPH BERENDES. Witnesses:

O'r'ro KoNIG, O'rro BUsoH,

It is easily soluble in alcohol and ether and issplit up into ethoxyacetic acid and menthol 2. The herein-described new ethoxy ace 'lyl Intestimony whereof I have hereunto set

